KR20040008162A - 신규한 프탈라지논 - Google Patents
신규한 프탈라지논 Download PDFInfo
- Publication number
- KR20040008162A KR20040008162A KR10-2003-7013937A KR20037013937A KR20040008162A KR 20040008162 A KR20040008162 A KR 20040008162A KR 20037013937 A KR20037013937 A KR 20037013937A KR 20040008162 A KR20040008162 A KR 20040008162A
- Authority
- KR
- South Korea
- Prior art keywords
- alkyl
- phenyl
- alkoxy
- tetrahydro
- cis
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
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- 150000001875 compounds Chemical class 0.000 claims abstract description 85
- -1 N-methylpiperidyl Chemical group 0.000 claims description 257
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 57
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 47
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 44
- 229910052736 halogen Inorganic materials 0.000 claims description 43
- 150000002367 halogens Chemical class 0.000 claims description 43
- 150000003839 salts Chemical class 0.000 claims description 34
- 125000004076 pyridyl group Chemical group 0.000 claims description 32
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 27
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
- 229910052731 fluorine Inorganic materials 0.000 claims description 19
- 239000011737 fluorine Substances 0.000 claims description 19
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 18
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 18
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 17
- 239000000460 chlorine Chemical group 0.000 claims description 17
- 229910052801 chlorine Chemical group 0.000 claims description 17
- 125000001153 fluoro group Chemical group F* 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 238000011282 treatment Methods 0.000 claims description 15
- 239000003814 drug Substances 0.000 claims description 13
- 239000005711 Benzoic acid Substances 0.000 claims description 12
- 235000010233 benzoic acid Nutrition 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
- 201000010099 disease Diseases 0.000 claims description 11
- 125000002883 imidazolyl group Chemical group 0.000 claims description 11
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 claims description 10
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
- 125000002541 furyl group Chemical group 0.000 claims description 9
- 125000001624 naphthyl group Chemical group 0.000 claims description 9
- 125000000335 thiazolyl group Chemical group 0.000 claims description 9
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 8
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 8
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 6
- 125000002971 oxazolyl group Chemical group 0.000 claims description 6
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 6
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 6
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 6
- 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims description 6
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- MALIONKMKPITBV-UHFFFAOYSA-N 2-(3-chloro-4-hydroxyphenyl)-n-[2-(4-sulfamoylphenyl)ethyl]acetamide Chemical group C1=CC(S(=O)(=O)N)=CC=C1CCNC(=O)CC1=CC=C(O)C(Cl)=C1 MALIONKMKPITBV-UHFFFAOYSA-N 0.000 claims description 4
- WKLKSQPDIITJAK-SJORKVTESA-N C1=C(Cl)C(OC)=CC=C1C1=NN(C=2C=CC(=CC=2)C(O)=O)C(=O)[C@@H]2[C@H]1CC=CC2 Chemical compound C1=C(Cl)C(OC)=CC=C1C1=NN(C=2C=CC(=CC=2)C(O)=O)C(=O)[C@@H]2[C@H]1CC=CC2 WKLKSQPDIITJAK-SJORKVTESA-N 0.000 claims description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 4
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 4
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 4
- 125000005592 polycycloalkyl group Polymers 0.000 claims description 4
- MAQRYDHZOWQDGA-CVEARBPZSA-N (4ar,8as)-2-(1,3-benzothiazol-6-yl)-4-(3-chloro-4-methoxyphenyl)-4a,5,8,8a-tetrahydrophthalazin-1-one Chemical compound C1=C(Cl)C(OC)=CC=C1C1=NN(C=2C=C3SC=NC3=CC=2)C(=O)[C@@H]2[C@H]1CC=CC2 MAQRYDHZOWQDGA-CVEARBPZSA-N 0.000 claims description 3
- OUKXFRRIGMEYDR-MSOLQXFVSA-N (4ar,8as)-4-(3-chloro-4-ethoxyphenyl)-2-phenyl-4a,5,8,8a-tetrahydrophthalazin-1-one Chemical compound C1=C(Cl)C(OCC)=CC=C1C1=NN(C=2C=CC=CC=2)C(=O)[C@@H]2[C@H]1CC=CC2 OUKXFRRIGMEYDR-MSOLQXFVSA-N 0.000 claims description 3
- NCSNHJSFGHSOCC-SJORKVTESA-N (4ar,8as)-4-(3-chloro-4-methoxyphenyl)-2-(1,3,4-trimethylpyrazolo[3,4-b]pyridin-6-yl)-4a,5,8,8a-tetrahydrophthalazin-1-one Chemical compound C1=C(Cl)C(OC)=CC=C1C1=NN(C=2N=C3N(C)N=C(C)C3=C(C)C=2)C(=O)[C@@H]2[C@H]1CC=CC2 NCSNHJSFGHSOCC-SJORKVTESA-N 0.000 claims description 3
- PNFAJRGVWRHMSV-MSOLQXFVSA-N (4ar,8as)-4-(3-chloro-4-methoxyphenyl)-2-(1-oxo-3h-2-benzofuran-5-yl)-4a,5,8,8a-tetrahydrophthalazin-1-one Chemical compound C1=C(Cl)C(OC)=CC=C1C1=NN(C=2C=C3COC(=O)C3=CC=2)C(=O)[C@@H]2[C@H]1CC=CC2 PNFAJRGVWRHMSV-MSOLQXFVSA-N 0.000 claims description 3
- RVNXAYVDPLDECT-PKTZIBPZSA-N (4ar,8as)-4-(3-chloro-4-methoxyphenyl)-2-[1-(4-methylphenyl)sulfonylpiperidin-4-yl]-4a,5,8,8a-tetrahydrophthalazin-1-one Chemical compound C1=C(Cl)C(OC)=CC=C1C([C@@H]1CC=CC[C@@H]1C1=O)=NN1C1CCN(S(=O)(=O)C=2C=CC(C)=CC=2)CC1 RVNXAYVDPLDECT-PKTZIBPZSA-N 0.000 claims description 3
- DTRSYKTUTDYBBR-UXHICEINSA-N (4ar,8as)-4-(3-chloro-4-methoxyphenyl)-2-[1-(morpholine-4-carbonyl)piperidin-4-yl]-4a,5,8,8a-tetrahydrophthalazin-1-one Chemical compound C1=C(Cl)C(OC)=CC=C1C([C@@H]1CC=CC[C@@H]1C1=O)=NN1C1CCN(C(=O)N2CCOCC2)CC1 DTRSYKTUTDYBBR-UXHICEINSA-N 0.000 claims description 3
- SLXNCDDRQHKYPZ-CABCVRRESA-N (4ar,8as)-4-(3-chloro-4-methoxyphenyl)-2-[6-methyl-3-(trifluoromethyl)pyridin-2-yl]-4a,5,8,8a-tetrahydrophthalazin-1-one Chemical compound C1=C(Cl)C(OC)=CC=C1C1=NN(C=2C(=CC=C(C)N=2)C(F)(F)F)C(=O)[C@@H]2[C@H]1CC=CC2 SLXNCDDRQHKYPZ-CABCVRRESA-N 0.000 claims description 3
- ZGBRFHWLOXQCMR-MSOLQXFVSA-N (4ar,8as)-4-(3-chloro-4-methoxyphenyl)-2-cycloheptyl-4a,5,8,8a-tetrahydrophthalazin-1-one Chemical compound C1=C(Cl)C(OC)=CC=C1C([C@@H]1CC=CC[C@@H]1C1=O)=NN1C1CCCCCC1 ZGBRFHWLOXQCMR-MSOLQXFVSA-N 0.000 claims description 3
- HZXQJGPDTRZCNX-CVEARBPZSA-N (4ar,8as)-4-(3-chloro-4-methoxyphenyl)-2-cyclopentyl-4a,5,8,8a-tetrahydrophthalazin-1-one Chemical compound C1=C(Cl)C(OC)=CC=C1C([C@@H]1CC=CC[C@@H]1C1=O)=NN1C1CCCC1 HZXQJGPDTRZCNX-CVEARBPZSA-N 0.000 claims description 3
- QFAHXLIVMRUENH-SJORKVTESA-N (4ar,8as)-4-(3-chloro-4-methoxyphenyl)-2-phenyl-4a,5,8,8a-tetrahydrophthalazin-1-one Chemical compound C1=C(Cl)C(OC)=CC=C1C1=NN(C=2C=CC=CC=2)C(=O)[C@@H]2[C@H]1CC=CC2 QFAHXLIVMRUENH-SJORKVTESA-N 0.000 claims description 3
- OPOCKICASWPPML-CVEARBPZSA-N (4ar,8as)-4-(3-chloro-4-methoxyphenyl)-2-quinoxalin-2-yl-4a,5,8,8a-tetrahydrophthalazin-1-one Chemical compound C1=C(Cl)C(OC)=CC=C1C1=NN(C=2N=C3C=CC=CC3=NC=2)C(=O)[C@@H]2[C@H]1CC=CC2 OPOCKICASWPPML-CVEARBPZSA-N 0.000 claims description 3
- 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims description 3
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
- HCNFONHPDDMXQF-SJORKVTESA-N C1=C(Br)C(OC)=CC=C1C1=NN(C=2C=CC(=CC=2)C(O)=O)C(=O)[C@@H]2[C@H]1CC=CC2 Chemical compound C1=C(Br)C(OC)=CC=C1C1=NN(C=2C=CC(=CC=2)C(O)=O)C(=O)[C@@H]2[C@H]1CC=CC2 HCNFONHPDDMXQF-SJORKVTESA-N 0.000 claims description 3
- SSIOKPPSQIDXIM-RTWAWAEBSA-N C1=C(Cl)C(OC)=CC=C1C([C@@H]1CC=CC[C@@H]1C1=O)=NN1CCCCOC1=CC=C(C(O)=O)C=C1 Chemical compound C1=C(Cl)C(OC)=CC=C1C([C@@H]1CC=CC[C@@H]1C1=O)=NN1CCCCOC1=CC=C(C(O)=O)C=C1 SSIOKPPSQIDXIM-RTWAWAEBSA-N 0.000 claims description 3
- SUVSLGXXBRXKFE-SJORKVTESA-N C1=C(F)C(OC)=CC=C1C1=NN(C=2C=CC(=CC=2)C(O)=O)C(=O)[C@@H]2[C@H]1CC=CC2 Chemical compound C1=C(F)C(OC)=CC=C1C1=NN(C=2C=CC(=CC=2)C(O)=O)C(=O)[C@@H]2[C@H]1CC=CC2 SUVSLGXXBRXKFE-SJORKVTESA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- MNLAVFKVRUQAKW-UHFFFAOYSA-N VR nerve agent Chemical compound CCN(CC)CCSP(C)(=O)OCC(C)C MNLAVFKVRUQAKW-UHFFFAOYSA-N 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 3
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 3
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims description 3
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000000332 coumarinyl group Chemical group O1C(=O)C(=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 3
- 125000001041 indolyl group Chemical group 0.000 claims description 3
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 3
- 125000001893 nitrooxy group Chemical group [O-][N+](=O)O* 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims description 3
- 125000004193 piperazinyl group Chemical group 0.000 claims description 3
- 125000005936 piperidyl group Chemical group 0.000 claims description 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 3
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 3
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 3
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000005493 quinolyl group Chemical group 0.000 claims description 3
- 208000023504 respiratory system disease Diseases 0.000 claims description 3
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 3
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 3
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- XGPYVDGLRMEDNA-MSOLQXFVSA-N (4ar,8as)-2-(1-acetylpiperidin-4-yl)-4-(3-chloro-4-methoxyphenyl)-4a,5,8,8a-tetrahydrophthalazin-1-one Chemical compound C1=C(Cl)C(OC)=CC=C1C([C@@H]1CC=CC[C@@H]1C1=O)=NN1C1CCN(C(C)=O)CC1 XGPYVDGLRMEDNA-MSOLQXFVSA-N 0.000 claims description 2
- UWFNLSOFRPEBAG-SJORKVTESA-N (4ar,8as)-4-(3-chloro-4-methoxyphenyl)-2-(1h-indazol-5-yl)-4a,5,8,8a-tetrahydrophthalazin-1-one Chemical compound C1=C(Cl)C(OC)=CC=C1C1=NN(C=2C=C3C=NNC3=CC=2)C(=O)[C@@H]2[C@H]1CC=CC2 UWFNLSOFRPEBAG-SJORKVTESA-N 0.000 claims description 2
- LMKVPAUGSCDEIT-KGLIPLIRSA-N (4ar,8as)-4-(3-chloro-4-methoxyphenyl)-2-(3-thiophen-2-yl-1,2,4-thiadiazol-5-yl)-4a,5,8,8a-tetrahydrophthalazin-1-one Chemical compound C1=C(Cl)C(OC)=CC=C1C([C@@H]1CC=CC[C@@H]1C1=O)=NN1C1=NC(C=2SC=CC=2)=NS1 LMKVPAUGSCDEIT-KGLIPLIRSA-N 0.000 claims description 2
- CKKOYCZNJZPSKC-MSOLQXFVSA-N (4ar,8as)-4-(3-chloro-4-methoxyphenyl)-2-(4-imidazol-1-ylbutyl)-4a,5,8,8a-tetrahydrophthalazin-1-one Chemical compound C1=C(Cl)C(OC)=CC=C1C([C@@H]1CC=CC[C@@H]1C1=O)=NN1CCCCN1C=NC=C1 CKKOYCZNJZPSKC-MSOLQXFVSA-N 0.000 claims description 2
- GWKHQPXIWZEUAG-MSOLQXFVSA-N (4ar,8as)-4-(3-chloro-4-methoxyphenyl)-2-[1-(2-oxoimidazolidine-1-carbonyl)piperidin-4-yl]-4a,5,8,8a-tetrahydrophthalazin-1-one Chemical compound C1=C(Cl)C(OC)=CC=C1C([C@@H]1CC=CC[C@@H]1C1=O)=NN1C1CCN(C(=O)N2C(NCC2)=O)CC1 GWKHQPXIWZEUAG-MSOLQXFVSA-N 0.000 claims description 2
- OVMYZTUABUPBOL-YADHBBJMSA-N (4ar,8as)-4-(3-chloro-4-methoxyphenyl)-2-[1-(pyridin-4-ylmethyl)piperidin-4-yl]-4a,5,8,8a-tetrahydrophthalazin-1-one Chemical compound C1=C(Cl)C(OC)=CC=C1C([C@@H]1CC=CC[C@@H]1C1=O)=NN1C1CCN(CC=2C=CN=CC=2)CC1 OVMYZTUABUPBOL-YADHBBJMSA-N 0.000 claims description 2
- KWSCKNOZSGEPOE-RPBOFIJWSA-N (4ar,8as)-4-(3-chloro-4-methoxyphenyl)-2-[4-[4-[2-(dimethylamino)ethyl]piperazine-1-carbonyl]phenyl]-4a,5,8,8a-tetrahydrophthalazin-1-one Chemical compound C1=C(Cl)C(OC)=CC=C1C1=NN(C=2C=CC(=CC=2)C(=O)N2CCN(CCN(C)C)CC2)C(=O)[C@@H]2[C@H]1CC=CC2 KWSCKNOZSGEPOE-RPBOFIJWSA-N 0.000 claims description 2
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- 125000002785 azepinyl group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 8
- APJAEXGNDLFGPD-AWCRTANDSA-N 3-amino-n-{4-[2-(2,6-dimethyl-phenoxy)-acetylamino]-3-hydroxy-1-isobutyl-5-phenyl-pentyl}-benzamide Chemical compound C([C@@H]([C@@H](O)C[C@H](CC(C)C)NC(=O)C=1C=CC(N)=CC=1)NC(=O)COC=1C(=CC=CC=1C)C)C1=CC=CC=C1 APJAEXGNDLFGPD-AWCRTANDSA-N 0.000 claims 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical group [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 2
- LFMFPKKYRXFHHZ-UHFFFAOYSA-N R24 Chemical compound C1=C(Cl)C(C)=CC=C1NC1=NC(N)=C(C=CC=C2)C2=N1 LFMFPKKYRXFHHZ-UHFFFAOYSA-N 0.000 claims 2
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 2
- 239000012876 carrier material Substances 0.000 claims 1
- 101100296720 Dictyostelium discoideum Pde4 gene Proteins 0.000 abstract description 9
- 101100082610 Plasmodium falciparum (isolate 3D7) PDEdelta gene Proteins 0.000 abstract description 9
- 239000003112 inhibitor Substances 0.000 abstract description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 56
- 239000000243 solution Substances 0.000 description 35
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 30
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
- 239000000203 mixture Substances 0.000 description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 239000007858 starting material Substances 0.000 description 21
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
- 239000002904 solvent Substances 0.000 description 16
- 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 description 15
- 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 description 15
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 15
- 235000019341 magnesium sulphate Nutrition 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 14
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
- IVOMOUWHDPKRLL-KQYNXXCUSA-N Cyclic adenosine monophosphate Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-KQYNXXCUSA-N 0.000 description 11
- IVOMOUWHDPKRLL-UHFFFAOYSA-N UNPD107823 Natural products O1C2COP(O)(=O)OC2C(O)C1N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-UHFFFAOYSA-N 0.000 description 11
- 229940095074 cyclic amp Drugs 0.000 description 11
- 150000003254 radicals Chemical group 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 210000004027 cell Anatomy 0.000 description 10
- 239000013067 intermediate product Substances 0.000 description 10
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Landscapes
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01110228 | 2001-04-25 | ||
| EP01110228.2 | 2001-04-25 | ||
| PCT/EP2002/004438 WO2002085906A2 (en) | 2001-04-25 | 2002-04-23 | Phthalazinones derivatives useful as pde4/7 inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20040008162A true KR20040008162A (ko) | 2004-01-28 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR10-2003-7013937A Withdrawn KR20040008162A (ko) | 2001-04-25 | 2002-04-23 | 신규한 프탈라지논 |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US7186710B2 (cs) |
| EP (1) | EP1385848A2 (cs) |
| JP (1) | JP2004526789A (cs) |
| KR (1) | KR20040008162A (cs) |
| CN (1) | CN1503792A (cs) |
| AU (1) | AU2002317733B2 (cs) |
| BG (1) | BG108294A (cs) |
| BR (1) | BR0209149A (cs) |
| CA (1) | CA2445233A1 (cs) |
| CZ (1) | CZ299347B6 (cs) |
| EA (1) | EA200301100A1 (cs) |
| EE (1) | EE200300514A (cs) |
| HR (1) | HRP20030868A2 (cs) |
| HU (1) | HUP0303998A3 (cs) |
| IL (1) | IL157908A0 (cs) |
| MX (1) | MXPA03009583A (cs) |
| NO (1) | NO20034773L (cs) |
| NZ (1) | NZ529221A (cs) |
| PL (1) | PL363312A1 (cs) |
| SK (1) | SK14342003A3 (cs) |
| WO (1) | WO2002085906A2 (cs) |
| ZA (1) | ZA200308930B (cs) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20030074817A (ko) | 2001-02-15 | 2003-09-19 | 알타나 파마 아게 | Ｐｄｅ4 억제제로서의 프탈라지논-피페리디노-유도체 |
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| KR100263494B1 (ko) | 1991-10-09 | 2000-08-01 | 헤르빅 폰 모르체 | 피리도피리다지논 및 피리다진티온 화합물 |
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| PT672031E (pt) * | 1992-12-02 | 2003-06-30 | Pfizer | Dieteres de catecol como inibidores selectivos de pde iv |
| DE19533975A1 (de) | 1995-09-14 | 1997-03-20 | Merck Patent Gmbh | Arylalkyl-diazinone |
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| WO1999031071A1 (en) | 1997-12-15 | 1999-06-24 | Byk Gulden Lomberg Chemische Fabrik Gmbh | New phthalazinones |
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-
2002
- 2002-04-23 EA EA200301100A patent/EA200301100A1/ru unknown
- 2002-04-23 CZ CZ20033206A patent/CZ299347B6/cs not_active IP Right Cessation
- 2002-04-23 BR BR0209149-6A patent/BR0209149A/pt not_active Application Discontinuation
- 2002-04-23 US US10/475,657 patent/US7186710B2/en not_active Expired - Fee Related
- 2002-04-23 IL IL15790802A patent/IL157908A0/xx unknown
- 2002-04-23 PL PL02363312A patent/PL363312A1/xx not_active Application Discontinuation
- 2002-04-23 SK SK1434-2003A patent/SK14342003A3/sk not_active Application Discontinuation
- 2002-04-23 AU AU2002317733A patent/AU2002317733B2/en not_active Ceased
- 2002-04-23 EP EP02747291A patent/EP1385848A2/en not_active Withdrawn
- 2002-04-23 CA CA002445233A patent/CA2445233A1/en not_active Abandoned
- 2002-04-23 JP JP2002583433A patent/JP2004526789A/ja not_active Withdrawn
- 2002-04-23 NZ NZ529221A patent/NZ529221A/en unknown
- 2002-04-23 CN CNA028087429A patent/CN1503792A/zh active Pending
- 2002-04-23 MX MXPA03009583A patent/MXPA03009583A/es unknown
- 2002-04-23 WO PCT/EP2002/004438 patent/WO2002085906A2/en active IP Right Grant
- 2002-04-23 HR HR20030868A patent/HRP20030868A2/xx not_active Application Discontinuation
- 2002-04-23 KR KR10-2003-7013937A patent/KR20040008162A/ko not_active Withdrawn
- 2002-04-23 EE EEP200300514A patent/EE200300514A/xx unknown
- 2002-04-23 HU HU0303998A patent/HUP0303998A3/hu unknown
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2003
- 2003-10-24 NO NO20034773A patent/NO20034773L/no not_active Application Discontinuation
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Also Published As
| Publication number | Publication date |
|---|---|
| PL363312A1 (en) | 2004-11-15 |
| EA200301100A1 (ru) | 2004-06-24 |
| CN1503792A (zh) | 2004-06-09 |
| NO20034773D0 (no) | 2003-10-24 |
| ZA200308930B (en) | 2004-06-09 |
| BR0209149A (pt) | 2004-07-13 |
| WO2002085906A2 (en) | 2002-10-31 |
| HRP20030868A2 (en) | 2005-08-31 |
| EP1385848A2 (en) | 2004-02-04 |
| US7186710B2 (en) | 2007-03-06 |
| CZ299347B6 (cs) | 2008-06-25 |
| IL157908A0 (en) | 2004-03-28 |
| WO2002085906A3 (en) | 2002-12-19 |
| US20040127707A1 (en) | 2004-07-01 |
| HUP0303998A2 (hu) | 2004-05-28 |
| CA2445233A1 (en) | 2002-10-31 |
| AU2002317733B2 (en) | 2007-12-13 |
| SK14342003A3 (sk) | 2004-05-04 |
| NO20034773L (no) | 2003-12-10 |
| NZ529221A (en) | 2005-04-29 |
| JP2004526789A (ja) | 2004-09-02 |
| CZ20033206A3 (cs) | 2004-02-18 |
| EE200300514A (et) | 2004-02-16 |
| MXPA03009583A (es) | 2004-02-12 |
| BG108294A (bg) | 2004-09-30 |
| HUP0303998A3 (en) | 2007-03-28 |
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